Molecular modeling of the interactions of glutamate carboxypeptidase II with its potent NAAG-based inhibitors

Journal of Medicinal Chemistry

Volumn 45, Issue 19, 2002, Pages 4140-4152

  Rong, Suo Bao ^a,b   Zhang, Jiazhong ^a   Neale, Joseph H ^c   Wroblewski, Jarda T ^d   Wang, Shaomeng ^a   Kozikowski, Alan P ^a  

^a GEORGETOWN UNIVERSITY   (United States)

^b Locus Discovery Inc   (United States)

^c GEORGETOWN UNIVERSITY   (United States)

^d GEORGETOWN UNIVERSITY MEDICAL CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 (PHOSPHONOMETHYL)PENTANEDIOIC ACID; 4,4' PHOSPHINICOBIS(BUTANE 1,3 DICARBOXYLIC ACID); GLUTAMATE CARBOXYPEPTIDASE II; METALLOPROTEINASE; METALLOPROTEINASE INHIBITOR; N ACETYLASPARTYLGLUTAMIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; ARTICLE; COMPUTER MODEL; DRUG POTENCY; ENZYME INHIBITOR INTERACTION; ENZYME MECHANISM; HYDROPHOBICITY; MOLECULAR MODEL; PREDICTION; STRUCTURE ACTIVITY RELATION;

AMINO ACID SEQUENCE; CARBOXYPEPTIDASES; DIPEPTIDES; ELECTROSTATICS; ENZYME INHIBITORS; GLUTAMATE CARBOXYPEPTIDASE II; GLUTARATES; HYDROGEN BONDING; LIGANDS; MODELS, MOLECULAR; MOLECULAR SEQUENCE DATA; MUTAGENESIS, SITE-DIRECTED; ORGANOPHOSPHORUS COMPOUNDS; PHOSPHINIC ACIDS; SEQUENCE HOMOLOGY, AMINO ACID; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0037068438     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm010561g     Document Type: Article

References (84)

1. Hydrolysis of the brain dipeptide N-acetyl-L-aspartyl-L-glutamate: Subcellular and regional distribution, ontogeny, and the effects of lesions on N-acetylated α-linked acidic dipeptidase activity
2. Quantitation of N-acetyl-aspartylglutamate in microdissected rat brain nuclei and peripheral tissues: Findings with a novel liquid-phase radioimmunoassay
3. The regional distribution of N-acetylaspartyl-glutamate (NAAG) and peptidase activity against NAAG in the rat nervous system
4. Folylpoly-γ-glutamate carboxypeptidase from pig jejunum. Molecular characterization and relation to glutamate carboxypeptidase II
5. Hydrolysis of the brain dipeptide N-acetyl-L-aspartyl-L-glutamate Identification and characterization of a novel N-acetylated α-linked acidic dipeptidase activity from rat brain
6. 3H]NAAG catabolism in vivo
7. Immunocytochemical localization of the N-acetyl-aspartyl-glutamate (NAAG) hydrolyzing enzyme N-acetylated α-linked acidic dipeptidase (NAALADase)
8. Localization and synaptic release of N-acetylaspartylglutamate in the chick retina and optic tectum
9. N-acetylaspartylglutamate catabolism is achieved by an enzyme on the cell surface of neurons and glia
10. N-acetylaspartyl-glutamate: The most abundant peptide neurotransmitter in the mammalian central nervous system
11. N-acetylaspartylglutamate selectively activates mGluR3 receptors in transfected cells
12. N-acetylaspartylglutamate activates cyclic-AMP coupled metabotropic glutamate receptors in cerebellar astrocytes
13. N-acetylaspartylglutamate inhibits forskolin-stimulated cyclic AMP levels via a metabotropic glutamate receptor in cultured cerebellar granule cells
14. 3H]-GABA release by metabotropic glutamate receptors, in primary rat cortical cultures
15. 3H]-DCG IV) binding to metabotropic mGluR2 receptor-transfected cell membrane
16. High concentrations of N-acetylaspartylglutamate and AMPA, kainate, and NMDA binding sites
17. Low concentration N-acetylaspartylglutamate suppresses the climbing fiber response of Purkinje cells in Guinea pig cerebellar slices and the responses to excitatory amino acids of Xenopus laevis oocytes injected with cerebellar mRNA
18. 3H]norepinephrine release from rat hippocampal slices
19. High concentrations of N-acetylaspartylglutamate (NAAG) selectively activate NMDA receptors on mouse spinal cord neurons in cell culture
20. N-acetylaspartyl-glutamate acts as an agonist upon homomeric NMDA receptor (NMDAR1) expressed in Xenopus oocytes
21. Abnormal excitatory neurotransmitter metabolism in schizophrenic brains
22. Abnormal excitatory amino acid metabolism in amyotrophic lateral sclerosis
23. N-acetylaspartate and N-acetylaspartylglutamate levels in Alzheimer's disease post-mortem brain tissue
24. N-acetylaspartylglutamate, N-acetylaspartate and N-acetylated alpha-linked acidic dipeptidase in human brain and their alterations in Huntington's disease and Alzheimer's disease
25. Reductions in acidic amino acids and N-acetyl-aspartyl-glutamate in amyotrophic lateral sclerosis CNS
26. Distribution of N-acetylaspartylglutamate immunoreactivity in human brain and its alteration in neurodegenerative disease
27. Regional brain levels of N-acetyl-aspartylglutamate: The effect of kindled seizures
28. Selective inhibition of NAALA-Dase, which converts NAAG to glutamate, reduces ischemic brain injury
29. N-acetylated alpha-linked acidic dipeptidase converts N-acetylaspartylglutamate from a neuroprotectant to a neurotoxin
30. Design, synthesis, and biological activity of a potent inhibitor of neuropeptidase N-acetylated-alpha-linked acidic dipeptidase
31. Design and pharmacological activity of phosphinic acid based NAALADase inhibitors
32. Activation of class II or III metabotropic glutamate receptors protects cultured cortical neurons against excitotoxic degeneration
33. Neuroprotective activity of N-acetylaspartylglutamate in cultured cortical cells
34. The inhibitory mGluR agonist, S-4-carboxy-3-hydroxy-phenylglycine selectively attenuates NMDA neurotoxicity and oxygen-glucose deprivation-induced neuronal death
35. Glutamate and the pathophysiology of hypoxic-ischemic brain damage
36. Protection against ischaemic neuronal damage by drugs acting on excitatory neurotransmission
37. Effects of NAALADase inhibition on responses of dorsal horn neurons after inflammation and neuropathy
38. Spinal N-acetyl-alpha-linked acidic dipeptidase (NAALADase) inhibition attenuates mechanical allodynia induced by paw carrageen injection in the rat
39. Inhibition of spinal N-acetylated alpha linked acidic diptptidase produces an antinociceptive effect in the rat formalin test
40. Prostate-specific membrane antigen: A novel folate hydrolase in human prostatic carcinoma cells
41. Prostate-specific membrane antigen: Evidence for the existence of a second related human gene
42. Prostate-specific membrane antigen is a hydrolase with substrate and pharmacologic characteristics of a neuropeptidase
43. Molecular cloning of a peptidase against N-Acetylaspartylglutamate (NAAG) from a rat hippocampal cDNA library
44. Isolation and expression of rat brain cDNA encoding glutamate carboxypeptidase II
45. Aminopeptidase from Streptomyces griseus: Primary structure and comparison with other zinc-containing aminopeptidases
46. Cloning and nucleotide sequence of the Vibrio proteolyticus aminopeptidase gene
47. Significance of prostate-specific membrane antigen (PSMA). A neurocarboxypeptidase and membrane folate hydrolase
48. Structure of membrane glutamate carboxypeptidase
49. Site-directed mutagenesis of predicted active site residues in glutamate carboxypeptidase II
50. The extracellular regions of PSMA and the transferrin receptor contain an aminopeptidase domain: Implications for drug design
51. The complete nucleotide sequence of the Pseudomonas gene coding for carboxypeptidase G2
52. Dual function glutamate-related ligands: Discovery of a novel, potent inhibitor of glutamate carboxypeptidase II possessing mGluR3 agonist activity
53. Neuroprotection produced by the NAALADase inhibitor 2-PMPA in rat cerebellar neurons
54. Design of remarkably simple, yet potent urea-based inhibitors of glutamate carboxypeptidase II (NAALADase)
55. The SWISS-PROT protein sequence database and its supplement TrEMBL in 2000
56. BEAUTY: An enhanced BLAST-based search tool that integrates multiple biological information resources into sequence similarity search results
57. CLUSTAL W: Improving the sensitivity of progressive multiple sequence alignment through sequence weighting, positions-specific gap penalties and weight matrix choice
58. Homology modeling with low sequence identity
59. The FSSP database: Fold classification based on structure-structure alignment of proteins
60. Jpred: A consensus secondary structure prediction server
61. Evaluation and improvement of multiple sequence methods for protein secondary structure prediction
62. Application of enhanced multiple sequence alignment profiles to improve protein secondary structure prediction
63. Conservation and prediction of solvent accessibility in protein families
64. PDBsum: A Web-based database of summaries and analyses of all PDB structures
65. PDBsum: Summaries and analyses of PDB structures
66. Enlarged representative set of protein structures
67. Selection of representative protein data sets
68. CHARMM: A program for macromolecular energy, minimization, and dynamics calculations
69. An all-atom empirical energy function for the simulation of nucleic acids
70. All-atom empirical potential for molecular modeling and dynamics studies of proteins
71. Zinc binding in proteins and solution: A simple but accurate nonbonded representation
72. Comparison of simple potential functions for simulating liquid water
73. Homology modeling, model and software evaluation: Three related resources
74. Automated docking using a lamarckian genetic algorithm and empirical binding free energy function
75. Numerical integration of the Cartesian equations of motion of a system with constraints: MD of n-alkanes
76. New spherical-cutoff methods for long-range forces in macromolecular simulation
77. Crystal structure of the hereditary haemochromatosis protein hfe complexed with transferrin receptor
78. Crystal structure of the ectodomain of human transferrin receptor
79. Crystal structure of carboxypeptidase G2, a bacterial enzyme with applications in cancer therapy
80. Crystal structure of Aeromonas proteolytica aminopeptidase: A prototypical member of the cocatalytic zinc enzyme family
81. The structure of the Aeromonas proteolytica aminopeptidase complexed with a hydroxamate inhibitor. Involvement in catalysis of Glu151 and two zinc ions of the cocatalytic unit
82. Streptomyces griseus aminopeptidase: X-ray crystallographic structure at 1.75 Å resolution
83. Stereochemistry of polypeptide chain configurations
84. Hydrolysis of the neuropeptide N-acetylaspartylglutamate (NAAG) by cloned human glutamate carboxypeptidase II